The Generation Gap Has Been Filled

By the time that I had turned forty-seven, I had begun to suspect that my determination to never get married had perhaps been ill-advised. I had a fine, secure job, yes, and I had dated a beautiful woman, exactly two months my senior, for the past twelve years. She didn’t need me for money; I had always made it a point to date intelligent, resourceful women, the women who I’ve always been attracted to. I was certain that there was no problem with the sex; my own appetite had actually grown stronger since I entered middle-age, and I knew I was pleasing her as well, with her love for sex outdoors, sex in her office. I enjoyed it too, untying her hair’s work bun on her lunch break and slipping her shoes off. She always wore pantyhose, though, which I never cared for. A small quibble. I suppose there were small quibbles with me too. I suppose there were a dozen small quibbles, a thousand niggling doubts, all of them revealing themselves and flipping me the proverbial bird as I read her note, which casually and with great candor explained why she was not at home, and was in fact in a different, unspecified nation with a 25-year old boy, her new paramour.

“And we’re not exactly married,” her note sneered.

Reading that message, I began to focus on those pantyhose of hers, grasping at her single damned fault. Fortunately, such examination also drew my attention to Sheila.

Ah, Sheila! A new face in the blank halls of my workplace! She always wore flat shoes, no pumps, no heels, you see. She always wore socks underneath those dress shoes, some small, cowering beneath the leather of her footwear, others cream-colored and bunched down above her ankles. Those were my favorite. Her legs were bare and beautiful when she wore skirts, which was often. She was slightly pale, her hair curly and falling in braids down to her shoulders. Glasses, never too much make-up, forty-three years old. Her face was always bright, though, usually grinning. She took the office directly next to mine, and I was smitten hearing her voice on the phone through the wall, a effervescent mass of fast speech, very fast, and it tickled me.

I began to invent excuses to talk to her, like the high school boy at his first job carrying dishes past a pretty, decade-older cook whom he has a crush on. I, in my advanced age, tried to be a little more tactful. We hit it off well, talking for far too long about pretentious films and the like. We began to take lunches together. On certain days, there’d be remarkably little to do at work, and she’d drift into my office door, and we’d chat away about anything, up to and including the weather and the state of disrepair the elevator was in, and other vital debates.

She’d flirt. Thank goodness, because it helped me out. We’re all very careful today in the workplace, but she put me at ease, talking about her ex-boyfriend. She was very much like me, except she and her ex had been together since she was in high school. They’d had two children, now 18 and 22. But he’d left her and the girls a year or so back. Unlike me, she thought of his good points. One day in particular, she confessed a particularly interesting tidbit.

“We had a great thing going,” she said, wistful, “You know, he’d even take hours off work to come to my office and… fool around.”

“Really?” I responded, “My old girlfriend used to do the same thing with me, on our lunch breaks.”

That got us started. Luckily the door to my office was closed, because we began a little competition, comparing our exploits during the workday in increasingly intimate detail. She made me breathless with her eye toward detail, revealing that he was extra frisky when she’d wear red panties, which naturally gave me the image of her standing around in her red panties, walking to the copy machine in red panties. Red panties and floppy cream socks. Not to be outdone, I simply had to reveal my own ex’s demands that I adore her feet. A power trip, now that I think of it. Shelia smiled in a peculiar way at that fact, and I knew she was as filthy a thinker as me, and that she could feel my lips on her toes, and that made me feel great.

Over the next week, we’d wait far too patiently for any excuse to stop unnecessary work, wander into conversations with each other, and get back to our new favorite topic. I told her of my ex’s appreciation for public sex, of fucking in the waves of the ocean while at the shore on vacation. She confessed that she’d never tried that before, but her and her boyfriend used to have a grand old time in tents while camping, and in cars while coming home from (and sometimes going to) work. She even confessed that after he left her, she’d enjoyed an affair with a college intern, a 20-year old boy during the summer, always at the office. This particularly interested me, as I had never experienced a relationship with a far younger lady, though I’d always deeply wanted to. Now I imagined her in her panties and socks, walking away from the copier, and into her office, and the arms of her naked young lover, his sexual prime bringing her to tears of rapture.

By the next week, we’d extinguished our stories, but remained interested in the general topic. We began to discuss more detailed pleasures. I learned, for example, that her ex’s penis was six-and-a-half inches, which made me grin, as I was well over seven. I told her of my appreciation of my old flame’s dress sense, and my distaste for pantyhose.

“Oh, I hate pantyhose,” she huffed, securing her position as a goddess upon the soil.

Finally, by Thursday afternoon of that week, we’d begun repeating ourselves, and she asked the question I’d been waiting for:

“Hey, why don’t you rub my feet, if you’re so good at it?”

I agreed that I should back up my words, and she sat on my desk, and put her shoes up onto my lap. They were black and shining, like a schoolgirl’s. I undid the laces, and slid them off. Her socks were short that day, and cherry red. I pulled them off quite slowly, and I could sense her smile widening. Her toenails were unpolished, her feet were very dainty and soft. I rubbed them all over, from ankles to soles. She groaned in happiness, and I increased the pressure. Before we knew it, the work day was over. I gathered all of my strength, and smooched her on the toes of her left foot, quite softly. She did not look at me at first, as she covered her feet, but I saw her beaming smile as she finished, and she quickly pecked my lips, and made me promise we’d do the same thing tomorrow.

On a side note, I masturbated that night for the first time in years, envisioning Shelia‘s panties being slowly lowered by her young, fantastically well-hung lover, who proceeded to tend to her every vulgar desire, at her demand, with her socks on the entire time. I’d not had an orgasm since the last time I’d made love to my ex, and the feeling was overwhelmingly good. I felt full of energy, and ready for the next day.

She started early that Friday, stopping by my office right before lunch. She was wearing sneakers with her skirt and blouse for casual day, and she was wearing those cream socks. We barely spoke as she propped her feet up, and I took an especially long time removing her footwear. After a brief rub, she suddenly turned around, and lied on my desk on her belly.

“Could you massage my back too?” she asked.

We only had a few minutes before lunch, but I obeyed, rubbing her shoulders through her blouse, as I shamelessly ogled her bare legs and the shape of her body underneath her skirt. I was very aroused when she told me to stop. She sat back up, and kissed me again, a bit longer, and told me she’d see me after lunch. She gathered up her sneakers and socks, and left, as I wondered if I should go out for lunch, or stay in the office and relieve my pleasures. I opted for lunch.

There was little work to be done that day, at least for me, so I waited and waited for her, growing more and more anxious. The slightest brushing against the door made me jump. Finally, at about 2:00 PM, she entered. Instantly, she sensed how unnerved I was. I grew more jumpy as she drew closer. She put her hands on my knees, leaned close to me, and said:

“You know, I really like you. I like you a lot.”

And she kissed me, and pressed her tongue into my mouth, and I responded, and we kissed for minutes at a time, her hands still on my knees, still leaning down at me. We’d stop, look at each other, her still in her glasses, and kiss again. Her phone suddenly rang from behind the wall. She stood up.

“Ok. I’m going to get that. Then I’m going to forward all my calls, and we’re going to fool around.”

She smiled brightly, and left to answer the call. I had little idea of what to do in the meantime. After a few minutes, I decided to simply take off my tie, perhaps get casual while ’fooling around’. I had just removed it when she reappeared at my office and shut the door tight.

“Wow. Getting undressed already!”

We both laughed for quite a while at that one.

“Ok… ok,” she sputtered, trying to control her voice, “Ok, I’m not a very promiscuous girl. So we’re only going to play today. So, we’ll just stop at our underwear, ok?”

I’m afraid I may have been too swift in throwing off my clothes. I should have made it more entertaining for her. At least I remembered to leave by dress pants for last, removing my belt before leaving myself standing in my red cotton briefs. I had quite an erection, and her face lit up upon seeing it, her cheeks blushing just a bit.

“Wow, you must do some running,” she said, correctly, “You look really nice.”

She kept staring at me, drinking me in as she slipped off those shoes and socks. She was very clever, very aware of how to drive a man mad, slowly pulling her blouse out of her skirt, then taking out all of her hair pins one by one, and letting them drop to the floor. She undid her skirt, and let it drop, her blouse hiding her underwear, but revealing more of her bare legs. Her thighs had a little natural cellulite from aging, but I found that to make her more natural, more desirable, and she was in very good shape regardless. She turned to face the door, and unbuttoned her blouse, then spun around and tossed it off her shoulders, revealing a lacy blue bra and panties, hugging her body perfectly.

She approached me, now blushing a deep red. She removed her glasses, and set them upon my desk. She climbed upon my lap in my chair, and we kissed like drunken college students, one long, wet, uninterrupted smack, as our hands explored our naked sides and backs. We finally stopped, and I glanced at the clock. Nearly fifty minutes had passed. Fortunately that left us more than an hour and half of fun.

We kept our promise. We did not remove our remaining clothing, nor did we have any sort of sex. We had a very good time never the less. She lied on her back and let me kiss her feet, sucking on each of her toes as she cooed. I lifted her legs in the air and licked them all the way from the cut of her panties at her thighs, up to her heels. He legs were very moist by the time I had finished. She sat up and kissed me very forcefully, then licked my nose with quick laps, then kissed her way down my stomach, and probed her tongue around my navel and back up my chest, allowing her clothed breasts to warm my aching penis inside my briefs. I made certain to knead and massage those breasts as I kissed her back and behind her neck. They were not huge, but very soft and supple, her nipples solid under the lace. We continued to kiss and lick every nook and cranny, barely avoiding orgasm several times, until it was 5:00 PM. She backed away.

“Saturday night. What are you doing?” she inquired.

I said I was not doing much.

“Ok, meet me by the lobby of Charles Mason College at 10:30, we’re going to have a good time, and you’re coming to my house afterwards, and we’re staying there until we go to work on Monday, got it?”

Charles Mason College was between both our homes. I lustily agreed, and she left. And I went home.

Saturday night, I arrived at the lobby door ten minutes early. She was already there, smiling at the students popping in and out. She looked unbelievable in a small blue party dress, showcasing her cleavage, and a good deal of flesh above her knees. She wore fancy white shoes. No socks at all. No glasses. She leapt into my arms, and we kissed several times before I put her down.

“Come on. We going to go dancing at the club around the block.”

The club was named ’Sam Ale’s’, and it was the popular college club in town. It was a big place, several levels high. Loud music, and packed with kids. We were the oldest there by decades. We stepped in and hit the floor, crowded with hundreds of students, most of them clearly intoxicated. We danced sober, mainly with each other.

Suddenly, the lights began to flash, and a particularly popular song began to play, ’Sex in the Club’. Sheila yelped:

“Oh, all right! This is the whole reason why we came!”

I noticed that the dancing was becoming rather odd. I tried to concentrate through the colored lights. I soon became aware of what was happening, and my jaw dropped. Everyone was stripping down to the bare essentials, young men and women all around me. I turned to see Sheila, as she happily unbuttoned her dress’ back, and casually let it drop to the club floor. She stepped out of her shoes, now clad in only bra and panties, again, very frilly and lacy. I could not make out the color through the lights. She began dancing and grinding to the beat, several male students taking great interest in her beautiful, mature form.

“Come on! Have fun!” she shouted.

Without really knowing what I was doing, I quickly threw my shirt over my head, and dropped my pants. As always, I was wearing briefs. My arousal was once again evident, if less so than before given the lack of light.

My attentions soon turned to a large gaggle of young ladies, bouncing and cheering me on, all of them down to their panties and tank-tops or t-shirts. As I danced, I saw Sheila surrounded by young men, all of them down to boxers or briefs, all of them dancing close as she shook her scantly-clad rear. A few of the girls smiled and danced closer to me, their many cheap perfumes in my nostrils, and I let the beat take me, and I felt their nude bellies with my hands and I moved. One smiled and ground her ass into my groin, her cheeks almost totally revealed save for her tiny thong. I responded in kind, and she squealed as her friends surrounded me, their drunken breath all over my naked torso as their bodies surrounded me. I looked again to my date, and she was leading a young man’s hands up to her breasts as she kissed him romantically as they danced. Another boy at her side, his very large penis evident from his shorts, ground against her body, and she turned to kiss him as well. I found this so intensely erotic.

I quickly turned around as I felt a girl’s hand stroking up and down the front of my briefs. She was delighted and mouthing something I could not make out, but I knew it was positive. She was a very pouty blonde with big lips and large breasts given her 4’10 frame. She gazed up at me with doe eyes. She could not be a single day over 20. I lifted her up, and she wrapped her legs tightly around my hips, my penis ground tightly between her boiling legs, right against her barely covered pussy. I swung her around, and we kissed. Her tongue moved too quickly, but she was young and drunk. I planted a huge kiss on her breast, through her shirt, of course, and put her down. She was instantly back to dancing, and now several of her friends were exploring the surface of my underpants, their hands rustling all over as I moaned in joy. In retaliation, I reached behind as many girls as I could, at least four or five, and I pinched and teased their asses and snapped the lips of their panties. I felt a velvet bra, soaking with sweat, on my back, and I turned to see a skinny, giddy girl with long hair behind me. I cupped her breasts in my hands and squeezed them as she kissed me, and I moved my hands down to enjoy her ass. I was certain that Sheila was having an even better time than me, and I had never felt so good in my life.

As the song wound down, all the girls began to jump and shake their rears. I caught a few of them swinging around, and kissed whatever flesh I could find. The tune ended, and several of them jumped up to kiss me, and I gladly responded. The busty little blonde hopped up to my ears and whispered:

“You are coming back to my dorm right fucking now. Don’t even get your clothes, just c’mon.”

I told her I had a date, and I turned and saw Sheila rapturously squeezing and kissing her latest dance partner.

“Aw, come ON,” the blondie whined, “I so want to fuck an older guy. Come on… I’ve got like a brick of pot in my room and I wanna fuck your brains out…”

I leaned down and softly kissed her and told her no again. She smiled sweetly and walked away, mouthing ’next time’ at me as she left.

I hadn’t moved much on the floor, so my clothes were fairly easy to find. Sheila was already dressed and beaming. She took my hand and we headed for the door. I noted that very few of the club kids bothered to put their clothes back on after that song.

As we hit the outside world, our ears and heads buzzing, she squeezed me tight.

“Well, I had a fantastic time… I’m soaking wet, you know,” she whispered, pecking my cheek.

I told her that I was feeling very good myself. I noticed that she was dropping small papers on the ground as we left.

“Oh, a few guys gave me their cell numbers. They actually keep pens and paper in their pockets and they all bent down to fish them out after the song. That’s so cute, don’t you think?”

I agreed, and we cuddled close as we walked, and we soon were at her front door. We entered eagerly.

She was in my arms as soon as the door shut, her dress wet from perspiration. We kissed for a few minutes, there in parlor, then she broke away and kicked her fancy shoes right off her feet across the rug. The room was very well furnished, with soft couches and pictures of Sheila and her daughters adorning the walls.

“Ok. Now show me what you showed all those little girls at the club.”

I eagerly complied. I had never put my clothes back on quite fully, so they were a breeze to take off.

“Mmm. Now show me what you were saving for me.”

I smiled as best I could, and slipped out of my underwear, revealing my nudity to her for the first time. My penis happily drank in the warmth of her home, and our previous kisses had made it fully attentive.

She playfully gawked at my organ, and licked her lips as she undid the back of her dress, and tossed it aside in a ball. Her bra and panties were a matching forest green, as I could see in the non-colored light of her home. She unsnapped her bra, and tossed it onto the pile. Her nipples were plainly erect; I imagined her still being aroused from the club. Her breasts were just as supple as I imagined them to be, and I ached to attend to them.

She then turned her back to me, and slowly stepped out of her panties, revealing a small birthmark on her right cheek, just above her thigh. Her ass was completely perfect to me, and I approached her and embraced her from behind and kissed her gently all over her shoulders and neck. She moaned as I grasped her breasts and teased her nipples with my fingertips, my penis pressing against the softness of her rear and the small of her back. I kept one hand stimulating her breasts, and ran the other down to her pussy. I felt trimmed, scratchy pubic hair. I gently entered her with my hand; she was very hot inside, and very wet. I teased the whole area of her pussy, and softly brushed against her clitoris. She gasped and turned around to kiss me.